Fumaric Acid → HCID 15925348, compound

HRID 704217Notes

Reaction equation

HRID 704217 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH:23]([CH3:30])[CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:11]=2[CH:10]=1)=S.C(O)(=O)/C=C/C(O)=[O:38]>C(O)(=O)C.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH:23]([CH3:30])[CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:11]=2[CH:10]=1)=[O:38]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 15925311HCID 15925311, compound

Product 1

HCID 15925348HCID 15925348, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

Mercuric acetate (0.80 g) is added to a solution of N-(3-fluorobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide neutral fumarate (1.30 g) in acetic acid (20 cc), and the mixture obtained is stirred for 20 hours at a temperature in the region of 20° C. The black suspension obtained is filtered on sintered glass plugged with celite and the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with ethyl acetate (100 cc) and the organic phase is washed successively with normal sodium hydroxide (2×20 cc) and distilled water (2×20 cc) and with aqueous sodium chloride solution (20 cc) and dried over magnesium sulphate. After filtration, the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and a crude yellow oil (0.90 g) is thereby obtained. This residue is dissolved in hot ethanol (3 cc) and treated with fumaric acid (0.25 g) dissolved in ethanol (2 cc). After 4 hours' cooling to 4° C., the crystallized solid is separated by filtration, washed with cold ethanol (2×5 cc) and then dried at 50° C. under reduced pressure (5 mm Hg; 0.7 kPa) to give N-(3-fluorobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide neutral fumarate (0.7 g), m.p. 165° C.

Workup

  1. customthe mixture obtained
  2. customThe black suspension obtained
  3. filtrationis filtered on sintered glass
  4. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  5. washthe organic phase is washed successively with normal sodium hydroxide (2×20 cc)
  6. distillationdistilled water (2×20 cc)
  7. dry with materialwith aqueous sodium chloride solution (20 cc) and dried over magnesium sulphate
  8. filtrationAfter filtration
  9. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  10. customa crude yellow oil (0.90 g) is thereby obtained
  11. temperatureAfter 4 hours' cooling to 4° C.
  12. customthe crystallized solid is separated by filtration
  13. washwashed with cold ethanol (2×5 cc)
  14. customdried at 50° C. under reduced pressure (5 mm Hg; 0.7 kPa)

Sources & evidence

ORD record
ord-6257a036eaa4418e948f777763f8e3fa
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…